SU245070A1 - METHOD FOR OBTAINING SIMPLE-COMPLEX ALKYL-0-CHLORARYL ETHYL ETHYLENE GLYCOLES OF FATTY ACID - Google Patents
METHOD FOR OBTAINING SIMPLE-COMPLEX ALKYL-0-CHLORARYL ETHYL ETHYLENE GLYCOLES OF FATTY ACIDInfo
- Publication number
- SU245070A1 SU245070A1 SU1231441A SU1231441A SU245070A1 SU 245070 A1 SU245070 A1 SU 245070A1 SU 1231441 A SU1231441 A SU 1231441A SU 1231441 A SU1231441 A SU 1231441A SU 245070 A1 SU245070 A1 SU 245070A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- fatty acid
- chloraryl
- glycoles
- ethyl ethylene
- complex alkyl
- Prior art date
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title description 3
- 239000000194 fatty acid Substances 0.000 title description 3
- 150000004665 fatty acids Chemical class 0.000 title description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-Chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-Chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing Effects 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 230000003000 nontoxic Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Description
Изобретение относитс к Способу получени новых соединений, которые могут быть использованы в полимерной промышленности.The invention relates to a method for producing new compounds that can be used in the polymer industry.
По предлагаемому способу синтез провод тAccording to the proposed method, the synthesis is carried out
взаимодействием о-хлорфенола, этиленхлоргидрина в присутствии 40%-кого раствора едкого натра и жирной кислоты в присутствии катализатора по схеме.by the interaction of o-chlorophenol, ethylene chlorohydrin in the presence of 40% sodium hydroxide solution and fatty acid in the presence of a catalyst according to the scheme.
СНгОНSNGON
RCOOH CHcrOCOR IС1RCOOH CHcrOCOR IC1
где R - алкильный радикал Сз-Ci2.where R is the alkyl radical of C3-Ci2.
Алкил-о-хлорариловые эфиры этиленгликол представл ют собой масл нистые, прозрачные , нетоксичные, без запаха жидкости, в воде не растворимы и хорошо растворимы в органических растворител х.Ethylene glycol alkyl-o-chloroaryl ethers are oily, clear, non-toxic, odorless, insoluble in water, and highly soluble in organic solvents.
Пример. Синтез пропинат-о-хлорфенилового эфира этиленгликол .Example. Synthesis of ethylene glycol propinate-o-chlorophenyl ether
В трехгорлую колбу, снабженную мешалкой , с краном в нижней части дл слива промежуточных продуктов по ходу реакции, термометром , капельной воронкой, водоотделителем , помещают 13 г (0,1 моль) о-хлорфенола, 4 г 40%-ного раствора едкого натра и нагревают 30 мин при 100-118°С. По капл м прибавл ют 9 г (0,11 моль) этиленхлоргидрина и нагревают 2-2,5 час при 90-95°С. Далее,In a three-necked flask equipped with a stirrer, with a valve at the bottom to drain the intermediate products during the reaction, a thermometer, an addition funnel, a water separator, 13 g (0.1 mol) of o-chlorophenol, 4 g of a 40% aqueous solution of caustic soda and heated for 30 minutes at 100-118 ° C. 9 g (0.11 mol) of ethylene chlorohydrin is added dropwise and heated for 2-2.5 hours at 90-95 ° C. Further,
охлажда колбу с содержимым до комнатной температуры, отдел ют из нижней части образовавшийс хлористый натрий и воду. Затем приливают 50 мл толуола, 8,14 г (0,11 моль) пропионовой кислоты и 3-4% серной кислоты . Пагревалие продолжают 2,5-3 час при ПО-115°С.cooling the flask with the contents to room temperature; the sodium chloride and water formed are separated from the bottom. Then 50 ml of toluene, 8.14 g (0.11 mol) of propionic acid and 3-4% of sulfuric acid are poured. Pagrevalie continue for 2.5-3 hours at PO-115 ° C.
Образовавшуюс воду в впде азеотропной смеси удал ют толуолом. По окончании реакции содержимое колбы охлаждают до комнатной температуры, обрабатывают слабым шелочным раствором, промывают водой до нейтральной реакции, отгон ют толуол и подвергают вакуумной разгонке. Выдел ют 15,9 г фракции, выкипаюшей в пределах 128-129°С 5 По этому способу синтезировано дес ть. представителей алкил-о-хлорариловых эфиров этиленгликол , физико-химические константы которых приведень в таблице. Т-, -Ппртмртичоппетрни 11 р с дм с I пс иирс1снил Способ получени простых-сложных алкило-хлорариловых эфиров этиленгликол и жирной кислоты, отличающийс тем, что о-хлор 6 фенол последовательно подвергают взаимодействию с этиленхлоргидрином в щелочной среде при кипении с выделением промежуточного эфира и с л ирной кислотой в присутстВИИ кислого катализатора и азеотропного аген д например толуола, при температуре кипени реакционной смеси с последующим выделением целевого продукта известными приемами .The water formed in the above azeotropic mixture is removed with toluene. Upon completion of the reaction, the contents of the flask are cooled to room temperature, treated with a weak silk solution, washed with water until neutral, toluene is distilled off and subjected to vacuum distillation. 15.9 g of the fraction were recovered, boiling away from 128-129 ° C 5 Ten were synthesized by this method. representatives of the alkyl-o-chloroaryl ethers of ethylene glycol, the physico-chemical constants of which are listed in the table. T-, -Prptmrtichoppetrini 11 p with dm with I ps iirs1nil A method for preparing ethylene glycol and fatty acid simple alkyl-chloroaryl ethers, characterized in that o-chloro 6 phenol is successively reacted with ethylene chlorohydrin in an alkaline medium at boiling with separation of the intermediate ether and with lactic acid in the presence of an acidic catalyst and an azeotropic agent, such as toluene, at the boiling point of the reaction mixture, followed by isolation of the target product by known techniques.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU245070A1 true SU245070A1 (en) |
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